Synthesis of the C22-C26 tetrahydropyran segment of phorboxazole by a stereoselective Prins cyclization

Authors
Rychnovsky, SD Thomas, CR
Citation
Sd. Rychnovsky et Cr. Thomas, Synthesis of the C22-C26 tetrahydropyran segment of phorboxazole by a stereoselective Prins cyclization, ORG LETT, 2(9), 2000, pp. 1217-1219
Citations number
43
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
2
Issue
9
Year of publication
2000
Pages
1217 - 1219
Database
ISI
SICI code
1523-7060(20000504)2:9<1217:SOTCTS>2.0.ZU;2-A
Abstract
Tetrahydropyran rings are found in many complex natural products, and the s egment-coupling Prins cyclization is an effective strategy for their synthe sis. We report a four-step, stereoselective synthesis of the C20-C27 tetrah ydropyran segment of phorboxazole. The key step is a Prins cyclization indu ced by catalytic BF3. OEt2.